


Five Times Dean Winchester Slept with a Guy and One Time He Didn't

by slidingkinsey



Category: Supernatural
Genre: M/M, Plot What Plot/Porn Without Plot, Stanford Era, kind of
Language: English
Status: Completed
Published: 2013-08-10
Updated: 2013-08-10
Packaged: 2017-12-23 00:46:12
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 8,700
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/920004
Author URL: https://archiveofourown.org/users/slidingkinsey/pseuds/slidingkinsey
Summary: <blockquote class="userstuff">
              <p>Dean is hunting on his own for the first time and this shit just keeps happening. And by "this shit", he means sex with men, but everything's much easier if he thinks of it as "this shit".</p>
            </blockquote>





	Five Times Dean Winchester Slept with a Guy and One Time He Didn't

**Author's Note:**

> gratuitous porn + my Big Queer Feelings about dean winchester + absolutely no research about settings or anything (except for some reason i made sure to look up what the admissions building at yale looked like because that was obviously essential)
> 
> thanks as always to eden22 for attempting to make sure i don't embarrass myself grammatically and whatnot.

Sedona, Arizona  
November 28, 2002

Dean did not have shit on this ghost. It wasn’t that none of the leads were panning out; it’s that there were no fucking leads. He couldn’t figure out a single reason why there would be a ghost attached to the library, and that is why he hates hunting alone, because research sucked. Sam should’ve been there. It was a haunted _library_ for fuck’s sake; it was perfect for him.

Dean pushed the thought away, because Sam was at Stanford and Dean was over that since Sam didn’t even call at Thanksgiving. He gulped down the dregs of what must have been his fiftieth cup of coffee at Mike’s fucking Diner. He needed to be out killing shit, not staring at the fucking laptop like he had been for the past four days. Well, except for when he went to the library and the records office and out to the bar a couple times. But he’d still spent so much time sitting in this booth he was pretty sure the seat was molded to his ass.

“More coffee?” the waiter asked, leaning against the other side of the booth and lifting the coffee pot.

“Yeah,” Dean said, glancing at his watch and wondering if he should just call it quits and go back to motel room. The waiter was the same one that’d been there every time he’d been in, and he didn’t seem to mind Dean sitting there for hours with his shitty laptop, although to be fair the place wasn’t ever close to full, except at dinnertime.

He watched the guy head back to the counter out of the corner of his eye, checked on the two old guys at the table by the door, and then turned back to his laptop. He decided he’d see if he could find any local historians, and then he could look them up tomorrow morning.  
He’d just finished up when the guys by the door got up and shuffled out, mumbling something to the waiter as they did. Dean checked his watch again and saw it was ten to ten, and shut his laptop.

The waiter walked up, and Dean assumed he was kicking him out, but the guy just dropped a piece of pecan pie onto the table by Dean’s elbow. Dean looked at it stupidly as the waiter hopped up on the end of the table and sat there, swinging his legs.

“I didn’t order pie,” Dean said. The guy was pretty small, and the way he was sitting made him look young somehow, even though Dean guessed they were about the same age.

“On the house,” the guy said, “Saw you looking at it earlier. Much like I noticed you staring at my ass. Repeatedly.”

“What?” Dean said, “I wasn’t—“

“Oh please,” the guy said, with just a hint of a smirk, “I’ve never seen you before, and then for the last four days you’re in here constantly, but only when it’s not busy. And the staring at my ass. You’re not exactly subtle.”

“I, uh,” Dean said, and tried again, “I’m a private investigator, I’m in town for a case, I’m staying at the motel across the road, and you have free wireless. So I’ve been coming over here to do research. Uh, I’m also straight.”

“Are you serious?” the guy said, looking pale.

“Yeah,” Dean said, and pulled on a shit-eating grin. “Sorry.”

“Huh,” the guy said, sliding off the table and turning to face Dean. “Well, I’m glad you’re not a total homophobe who wants to kick the shit out of me for hitting on you, especially since I waited until everyone was gone.”

“Yeah, does your boss approve of you giving free pie to strange men?”

“Actually, I own the place, so I can give pie to as many strange men as I want,” the guy said, grinning back.

“Mike?” Dean asked.

“Oh, no,” the guy said, “Mike’s my uncle. He sold me the place and retired to Florida. I’m Dev.”

“Dean.”

Dev looked at him for a moment, and then slid into the other side of the booth. “So, cheating husband or cheating wife?”

“What?”

"That’s what people hire P.I.s for, right?”

“Hey, I could be up to some Sherlock Holmes shit, here.”

“Oh?”

“Yeah. I promise not to do coke if I get bored, though.”

Dev’s eyebrows shot up. “You’re a fan?”

“Nah,” Dean said, “Well, not really. Just have a geeky kid brother.”

“Lucky,” Dev said, still grinning lazily. “I have a born-again Christian kid brother.”

Dean smiled down at the pie. “So can I still eat this, or is this purely getting-in-my-pants pie?”

“Eh, go ahead,” Dev said, waving one hand. “I _guess_ it’s not your fault that you’re straight. I’m just going to clean up, then I’m kicking you ass out.”

Dean grinned and devoured the pie, while Dev mopped and then disappeared into the back. Dean left a ten-dollar bill on the table and walked across to the motel.

He went back the next afternoon, once he’d seen the history buffs. He was pretty sure he had a line on the ghost, but he had to wait until dark to dig the bastard up.

“You’re in a good mood,” Dev said, flipping his mug over and filling it with coffee. The only other people in the diner were a group of what look like retired women a few booths down who were laughing outrageously at something.

“Got a break in the case.”

Dev raised an eyebrow at him. “Do P.I.s actually talk like that, or are you just trying to sound cool?”

Dean shrugged, gulping down the scalding coffee. “Got any more pie?”  
“Blueberry.”

“Hell yeah.”

“Alright, but it’s going on your bill this time. I can’t afford to be giving free pie to every pretty face that comes through if they’re not going to put out.”

Dean was working on a comeback, but then Dev was already walking away. He kind of had a swishy walk, Dean thought, or maybe it just looked that way because of the apron.

Dean ate his pie and then ordered a cheeseburger, because it was basically dinner time, and Dev called him a five-year-old for eating dessert before dinner. Then Dean figured he might as well just hang out there until it got dark, and once the dinner rush left and Dean was the only one there, Dev slid into the other side of the booth again and started telling Dean all about his mom and dad and how his mom was back in Gujarat right now for a wedding, and how many Led Zeppelin songs were actually supposed to be references to the Lord of the Rings and how some others just kind of seemed that way if you squinted. And he asked enough questions that Dean found himself telling Dev a couple of hunting stories disguised as investigations, and even a little bit about his mom.

Dev climbed out of the booth when a couple of truckers came in looking for a late supper, and once the streetlights flickered on Dean headed out, waving to Dev on his way to the door.

Digging graves was another thing that sucked about hunting alone. And then, when Dean burnt the bones, the fucking ghost couldn’t even be bothered to show up, so now he had got to hang around and make sure no one else started bleeding from the ear in the reference section, just in case he desecrated the wrong grave or something.

The next morning he was at the diner before it opened, because he was in dire need of a breakfast that would make him feel better about his hangover and his hamstrings. Dev caught sight of him when he came to the door to flip over the “Closed” sign, and immediately stuck his head out.

“Is that your car?” Dev said. “Yeah,” Dean said, grinning.

“Shit, if I’d have known that I would have tried to seduce you with more than pie.”

Dean snorted. “You like classic cars?”

“Well, I mean, I know shit all about them, but they’re sexy. You here for breakfast?”

“If I don’t eat something greasy, I’m gonna die,” Dean said, sliding off the hood and walking over to the door.

“One Lumberjack’s Breakfast, coming up,” Dev said, heading for the kitchen.

Dean took his usual booth. The place was empty, but it was Sunday so he figured there’d be a church crowd in a bit.

He got up and went over to the swinging doors behind the counter. “Is there a cook back there or just you?” he called, pushing one of the doors open.

“Just me,” he heard Dev say. “Why?”

“Thought I could keep you company?” Dean said, walking back into the kitchen.

Dev looked at him with raised eyebrows. “Sure, just stay over there,” he said, gesturing to one side of the kitchen, away from the stoves. Whatever he was cooking on the grill smelled delicious, and the radio was playing quietly. Dean leaned against the counter as Dev turned back to the grill and started flipping pancakes.

Dean could see, objectively, that Dev might be attractive. He was kind of built for a little guy. And he had, like, good bone structure or something. Lots of guys probably wanted to fuck him.

“So you’ve had gay sex?” Dean said.

Dev glanced at him over his shoulder. “Is that your idea of light dinner conversation?”

“It’s breakfast,” Dean pointed out.

“Right, I forgot,” Dev said, stretching up to grab a couple of plates. “Bicuriosity is as much a part of breakfast as bagels are.”

“I’m not bicurious!” Dean said.

“You just want to know what it’s like to fuck men,” Dev said, shoving a plate piled with food into Dean’s hands and pointing towards the cutlery.

“Do you, uh, do you actually _fuck_ men?” Dean said, mouth full of fried egg and toast.

“You mean do I stick my dick in them?” Dev said, hopping up on the counter across from Dean with his own plate in his lap. “I hope you at least understand that gay sex is not just some macho guy fucking some twinky guy in the ass, forever and ever amen.”

“So educate me!” Dean said. “Maple syrup?”

“Over there. Some guys top. Some guys bottom. Some guys switch. Some guys have no interest in anal sex. People are different. You don’t assume every girl you sleep with likes the exact same thing in bed.”

“Huh,” Dean said, shoving bacon in his mouth.

“And I don’t go around asking straight people how they fuck, so there’s that too.”

“So I should stop asking lesbians how they have sex?”

“You know you’re an ignorant asshole, right? And chew with your mouth closed, for fuck’s sake.”

Dean rolled his eyes. “So what if I was?”

“What if you were what?” Dev asked, buttering a piece of toast.

“I don’t know,” Dean said. “Bicurious. Staring at your ass the other day.”

Dev looked up at him. “Well,” he said, “I guess I would help you _satisfy_ that curiosity.” He winked absurdly and then smiled.

“Cool,” Dean said, and by the time he had crossed to where Dev was sitting, Dev had set his plate aside and spread his knees so Dean could step right between them and kiss him.

It was pretty much exactly like kissing a woman. Not that women all kissed the same, but Dean had kissed a lot of women and some of them kissed like this. Maybe sometimes there was more stubble or something.

Dev hitched his legs up around Dean’s hips and dragged him in. Dean put one hand down on the counter so he could lean forward, and, yeah, that was probably definitely a dick.

The little bell on the front door jingled. Dean stopped and glanced at Dev.

“We should probably not actually have sex in the kitchen anyways, “ Dev muttered, pushing him back gently. “Go out the back. Come back at closing time. If you still want.”

“Okay,” Dean said, licking his lips, “I’ll see you.”

Dev smirked at him, pulling an apron on over his head and heading for the doors.

Dean was unlocking the Impala when his phone rang, and of course, there was another dead guy in the library, except the deputy happened to mention that this guy was reading the same book as a couple of the other victims.

“What’s the book?” Dean asked.

“It’s a book of poetry by a local author, Vincent Michaels. It’s been pretty popular since he died last year. You know how it is with a violent death like that, people get curious.”

“Right,” Dean said, trying not to let the relief bleed into his voice. He would go get the book and burn the fucker along with the bones, just to be sure.

“I’ll let them know you’re on your way, Agent Smith.”

“Thanks, Deputy Lee. I really appreciate it.”

By the time Dean managed to sneak the book out of the library and found out where Michaels was buried and dug up the grave and fought off the asshole ghost and burnt everything and got cleaned up in a truck stop bathroom, it was almost eleven.

“Fuck,” he said, and started driving toward the diner anyways. He was a few blocks away when he recognized Dev walking along the sidewalk and pulled over, heart jumping into his mouth.

“You’re late,” Dev said, once Dean had finished rolling down the passenger window.

“I know,” Dean said.

“Holy shit,” Dev said, leaning in and frowning, “What happened to your face?”

Dean grimaced. “Got thrown into a lamppost. It’s nothing. And anyways, the case is closed. Finished. Let me drive you home?”

“Fine,” Dev said, opening the door and sliding into the passenger seat. “Keep going to Hall Street, then make a left.”

Dean nodded and turned the Impala around, grinning. “What?” Dev asked.

“Nothing,” Dean said.

“What?”

“You _waited_ for me.” “Shut up.”

“For almost an _hour_.” 

“Shut _up_.”

“You want me so bad,” Dean said, and immediately regretted it, glancing over at Dev worriedly.

Dev snorted. “Has anyone ever told you you have an ego problem?” he said, sliding a hand across Dean’s thigh.

“I’m about to have a concentration problem,” Dean muttered, turning onto Hall Street.

“Fifth house on the right,” Dev said, taking his hand away and leaning back against the seat. “The one with the big tree.”

“Here?” Dean asked, slowing to a crawl and pulling over. “Yeah.”

Dean turned the car off and glanced over at Dev. “I’m leaving town tomorrow.”

“So we should probably have sex now, then,” Dev said, getting out of the car. Dean followed him up to the front door and into the hall.

“Your face looks like shit,” Dev said, kicking off his shoes and staring at him.

“Thanks,” Dean said.

“Next time you should probably try to not get your ass kicked.” 

“I’ll keep that in mind.”

Dev grinned. “Bedroom’s this way.”

Dean followed him down the hall, peering into the living room as they went by. It was nice. Not nice like Dean felt uncomfortable though. The furniture looked older, maybe second-hand, just well taken care of. There were a bunch of pictures of what Dean assumed were family and friends on one wall, and a big screen TV with some kind of a gaming system. The DVD case for _Die Hard_ was sitting on the coffee table and Dean grinned.

The bedroom was nice too. Messy like Dean though his room might be if he didn’t live out of bags.

“C’mon,” Dev said, dropping down onto the bed. Dean crawled up over him and kissed him, working his shirt up slowly.

Dev fumbled at the button of his jeans and got them open. “Off,” he muttered, breaking away from Dean’s mouth for a minute. Dean half- pushed, half-kicked them off, pulling Dev up with his other hand and stripping his shirt off. Dev grabbed his ass and pulled him back down, rubbing up against him, and Dean leaned in to kiss his neck.

Dev laughed breathily and flipped them. Dean reflexively opened his legs as they settled so Dev could kneel between them, and then closed his eyes.

“Hey,” he heard Dev say. A hand rested lightly on his knee. “You okay?” 

“Yeah,” Dean said, opening his eyes. “Um, what are you going to do?”

“I was going to go down on you,” Dev said, still smoothing his hand over the side of Dean’s knee. It felt nice. He’d wrenched the tendons in that knee a couple times. “But only if you want, Dean.”

“No, I—I want that. You.”

“Okay,” Dev said, grinning and stripping his own pants off quickly before kneeling again and pressing his open mouth against Dean’s briefs.

“What the fuck,” Dean muttered, arching up as Dev sucked on his balls through the fabric. “Uh, take them off, take them off.”

Dev licked up his shaft once more, and then leaned up to kiss him sloppily while he dragged Dean’s boxers down around his knees, shifting so that he was straddling Dean’s legs. He moved back down Dean’s body slowly, and finally put his mouth on Dean’s dick. Dean’s legs flexed involuntarily, half-trapped under Dev.

“You’re really fucking hot,” Dev muttered, sliding off momentarily, and wrapping slick fingers around the base of Dean’s cock. “Can’t wait to see you come.”

“Shit,” Dean said as Dev took him in his mouth again. Dev slipped a hand under his ass and pushed up, encouraging him to arch up into his mouth. Dean moved with it, groaning as the head of his dick brushed against the inside of Dev’s cheek.

“I should—do you—“ Dean gasped out. Dev slid up his body again, kicking his own underwear off and pushing their dicks together. “This okay?” he asked breathlessly, curling his hand around both of them.

“Yeah,” Dean said, thrusting up.

“Ha,” Dev said, licking into his mouth as he started to roll his hips down. Dean bit hard at Dev’s lower lip and shifted, trying to get better leverage, and ended up with his legs hooked together behind Dev’s back.

“Uh huh, uh huh,” Dev said, panting wetly against Dean’s neck.

“Shit, Christ, fuck,” Dean said and came hard as Dev’s thumb pressed against the head of his dick. He managed to get a hand between their bodies and jerked Dev roughly, shuddering, until Dev half-laughed, half- moaned, and came across his stomach.

Russell, Kansas  
May 18, 2003

Dean liked women. There had been that one other thing, but it wasn’t a big deal. It was just something that happened. Once. It was like one gay drop in an ocean of straight. Dean had met gay guys, and he’d been in a few gay bars. That wasn’t him.

But when he’d driven by the bar, it looked just like a place he might go. A bit of a dive. People who were hot in the probably-lived-in-a-trailer-for- part-of-their-lives way standing outside smoking or talking to other people that were smoking. A sign that said “JUKEBOX!” taped to the inside of the window. Except it was called The Back Door and there was a Pride flag next to the jukebox sign.

So he thought he go in, and he’d know for sure that it wasn’t just the glitter or the ten dollar drinks or the way everyone took their shirt off for no reason. He already knew, but this would be, what did Sam used to say, _confirmation_.

It was dim inside, and he bought a pitcher of shitty beer and sat in a tiny booth at the back near the jukebox. Guns ‘n’ Roses was playing. There was a fucking pool table. There were two women slow dancing on the tiny dance floor, but no one gave a shit.

Dean gulped down half a glass of beer.

Once he looked around a bit, he could see most people were there in couples. The women on the dance floor. The two bearded guys drinking beer together at the bar. The group of four guys clustered around the pool table, and the two people hunched over their drinks in the booth nearest the door.

Then Dean accidentally made eye contact with one of the young guys sitting alone at the bar. “Shit,” he muttered, looking down quickly at his beer, but he could tell the guy was getting up. And coming over. And sitting down on the other side of the booth.

“Just passing through?” the guy said. He had one of those voices that’s lower than you expect it to be.

“Yep,” Dean said, glancing up at him. He looked like any guy Dean had ever talked to in a bar, leather jacket over a denim work shirt, short hair, five-o’clock shadow that was actually nine-o’clock shadow because a workday is twelve hours, not eight. Dean would bet the Impala he was wearing steel-toed boots. When he leaned forward and offered his hand, Dean could smell engine oil.

“Jake.”

“Dean,” Dean said. His hands were calloused and Dean knew those hands because they were his hands and he thought he might be panicking.

“D’you top?” Jake asked. He looked younger than Dean, by just a bit. Maybe twenty, twenty-one.

“Yeah,” Dean found himself saying.

Jake looked down at the table, rubbing his thumb along the edge. “D’you wanna get a motel room?”

“Sure,” Dean said, “Wanna help me finish this beer first?”

Jake drank the end of whatever was in his glass and filled it from the pitcher.

“So what do you do, Jake?” Dean asked, feeling awkward. “Maintenance at the plant on Alfred,” Jake said, “You?”

“Mechanic,” Dean says, because it’s a lie he can spin like a pro, and because it’s a lie his dad used to tell in bars like these. Except they had names like Jerry’s Lounge, and pride was either blue-collared and red- necked, or in short supply.

Jake nodded. “Where you from?”

“Kansas, actually,” Dean said, and then lets himself have a piece of honesty and adds, “Lawrence.”

“I know it,” Jake said, nodding again. “There’s a place we can go, a bit out of town. The Raleigh Motel. Room fourteen. I’ll meet you there.” Jake stood up and walked out of the bar.

Dean finished his beer slowly and did not panic. There had been that girl in South Carolina who had wanted to have sex but not lose what she thought of as her real virginity.

The Raleigh Motel was kind of a piece of shit on the side of the road. The parking lot had only a few cars, but there were a bunch of semis parked around back and in the field behind the office.

Dean walked over to room fourteen and knocked. He heard someone on the other side, and then the chain rattled and Jake opened the door. He was wearing a towel and his hair was damp. He jerked his head at Dean and opened the door wider.

Dean stepped inside and immediately took off his coat, feeling overdressed.

“This is how I do this,” Jake said. “I prep myself. You can watch and jerk it, or whatever. Then you fuck me on my hands and knees. Then I shower and I leave. You understand?”

Dean looked at the tension in Jake’s shoulders and the grip he had on the towel around his waist. “Got it,” Dean said, taking a half-step back as he pulled off his shirts.

Jake turned towards the bed, dropping the towel and grabbing a tube off of the cheap coverlet. Dean toed off his boots and socks and leaned against the wall next to the bed, watching Jake coat his fingers in lube before climbing onto the bed on his hands and knees.

“Condoms are on the table,” Jake said, and then pushed a finger inside himself.

“Kay,” Dean said, not sure if he should look or not, but Jake was already working another finger in beside the first and it was hard to not watch and think that his dick was going to replace those fingers. The fingers that Jake was now grinding back onto, panting, while he pulled them slowly in and out. Dean felt like it had to hurt, it had to hurt, but Jake was making all these jerky movements and when he pulled his fingers out to add more lube, Dean tugged absently at his jeans.

“Take it out,” Jake said, turning his head so that he was staring at Dean as he slid the two fingers back in. “Leave your jeans on,” he added.

Dean dragged down the zipper and shoved his underwear down enough to curl and hand around his cock and pull it out. He stroked lazily as he watched Jake add a third finger.

“Gonna fuck me,” Jake said pressing his fingers all the way in and twisting his hand. “Oh God. Condom.”

Dean scrabbled for one of the packets on the table and slid the condom on a little shakily.

“Lube,” Jake said, thrusting his fingers roughly. Dean slicked up and climbed onto the bed behind Jake.

“Do it,” Jake said, pulling his fingers out and bracing himself with both arms. “Do it, fuck me.”

Dean pressed the head of his dick in slowly, paused, and then pushed the rest of the way in equally slowly.

“More lube,” Jake said, voice muffled against the bed. Dean pulled out partway, coated his dick with lube and pushed back in slowly. He did it once more, and then Jake lifted his head up and said, “Now fuck me hard.”

Dean pushed in and out once, a bit faster, and then Jake shoved himself back onto Dean’s dick and growled, “Harder.”

Dean grabbed him by the hip and the shoulder and snapped his hips forward as he dragged Jake back, and Jake said, “Yeah,” so he did it again. And when Jake started squirming and rolling his hips under him, Dean dug his toes into the mattress and sped up. The bed was squeaking and Dean had the sudden feeling that he was actually in a porno, especially when Jake started fisting his own dick and muttering the filthiest things—“harder, fuck...your cock, God, want you to fucking come in me...right there, _God_ , right there...so bad”—that Dean could barely make out over the sound of his own breath, which was rasping in and out of his throat like he’d just gone three rounds with a werewolf, and Dean wasn’t one of those jerks who went on about how tight a girl was or not, because who gave a shit, but it was so _tight_.

Dean came, losing his rhythm as his foot slipped, and then because he wasn’t sure about anal sex etiquette, stayed still while he slowly softened and Jake’s movements became more frantic. When Jake tightened around him he jerked back instinctively, oversensitive, and Jake rolled off the bed easily and walked slightly shakily to the bathroom. As the door shut Dean tossed the condom in the little garbage can by the bed and looked down at the coverlet guiltily, silently apologizing to whoever had to clean that up. He got up and reached for his shirts.

Somerville, Massachusetts  
February 2, 2004

The third time was basically an accident. Dean had just wasted the poltergeist that had been haunting Will’s house, and Will had picked himself up, looked around at the totally destroyed kitchen, and said, “I could really use a drink.”

So they went to a bar just around the corner, because Dean could also use a drink, except the place Will took them was more like a restaurant, which Dean guessed was fair because the guy’s kitchen was trashed. So they had burgers, and beer, and Dean trotted out a few funny hunting stories, because he always forgot what a relief it was to not have to pretend to be something else. And Will laughed and asked a bunch of questions and launched into his own convoluted story about a deranged seagull and some guy in his office who Will hated because he actually made air quotes whenever he said “affirmative action”. Like they were just two guys, trading work stories, perfectly normal.

It wasn’t until Will insisted on paying the bill that Dean realized that their feet were pressed together under the table and they had kind of been sharing food and there was a definite date-vibe going on.

Dean didn’t do dates. And if he did, he knew when it was happening. But when Will knocked his shoulder against Dean’s as they walked into the parking lot and said, “Bedroom’s not trashed,” looking a little shy, Dean was kind of back on familiar ground. And Dean wasn’t sure what to do except walk back to Will’s, so they walked back to Will’s, and Will stayed over on the other side of the sidewalk except when they passed a women walking a black lab, and Dean knew they just looked like two guys leaving the bar. Neighbours, maybe, if you didn’t look too close.

The bedroom was basically intact, although a few pictures had fallen off the wall, and they cleaned up carefully. Will took the glass downstairs while Dean turned on the lamp and pulled the blinds down, and Will shut the door behind him before pressing Dean up against the wall and kissing him.

Dean let himself rest against the wall and wrapped his arms around Will’s back. He was a bit taller than Dean, wiry and fit in a home-gym kind of way, and his tongue was everywhere, one hand working down the back of Dean’s pants and the other holding his head in place firmly.  
Dean fisted a hand in Will’s shirt and sucked on his tongue, and then his lip. Will pressed a knee between Dean’s legs and kissed sloppily down the side of Dean’s neck, pulling his shirt out of the way as he went. Dean glanced at the bed, and shifted so that he was basically riding Will’s thighs. He yanked Will back up to kiss him again and started fumbling open the buttons on Will’s shirt.

“Can I suck you?” Will said, working Dean’s belt open between them.

“Fuck yeah,” Dean said, getting the last of the buttons open and pushing the shirt partway off Will’s shoulders.

“Should I be using a condom?”

“I’m clean,” Dean said.

Will dropped to his knees and yanked Dean’s jeans and underwear halfway down his thighs. Dean pushed his hips out from the wall as Will licked one palm and then sank down on Dean’s cock, bobbing and sucking and sinking lower until Dean felt Will’s throat fluttering around the head and he slapped both hands flat against the wall. Will was jerking whatever part of Dean’s dick wasn’t in his mouth, and his other hand was  
stroking Dean’s balls and pressing against the space behind them, and Dean didn’t really like how practiced it all felt except Will was drooling down the length of his cock and sinking even lower and mostly he was focusing on not coming.

Will deep-throated him and swallowed. “Shit,” Dean said, brushing his fingers across Will’s temple, “Going to—“

Will pulled off and straightened up without pausing the movements of his hands, and Dean came all over his neck and chest.

“Fuck,” Dean said weakly. Will huffed a laugh, peeling his shirt off and using it to clean himself off. He stood up and pulled off his jean and boxers, stepping back and flopping down on the bed. “Gonna reciprocate, here?” he asked.

Dean stepped forward, licking his lips. “I’ve never, uh...”

Will blinked, looking surprised, then shrugged. “Just watch the teeth,” he said, “And don’t try to be too hardcore.”

“Okay,” Dean said, climbing onto the bed while Will pushed himself up against the headboard. “Just—tell me if I’m fucking up.”

Will ran his hands down Dean’s back. “It’ll be good.”

Dean licked his palm and stroked Will a few times, getting used to the angle, thinking of blowjobs he’d had, and then bent down to lick up and down the underside of the shaft. Will sighed and dropped his head back against the wall, letting his hands drift to rest gently on the back of Dean’s neck and head.

Dean took the head in his mouth, careful to keep his teeth out of the way, and slid down as far as he could—not far—and sucked. It was weird to feel the foreskin moving under his lips, but other than that it was pretty much like he thought it would be. He stroked his hand up to meet his lips, twisting a bit, and found a rhythm, hand and mouth moving up and down together. He could tell it was good but not awesome, and he felt like a teenager going down on a girl for the first time. His jaw started to ache just like it had then too. He took advantage of the times his mouth slid off on the upstroke to lick and kiss at the spot right under the head, and sucked harder as he slid down until Will’s hands were flexing in his hair and he was making quiet noises.

“Let me come in your mouth?” he asked.

“Okay,” Dean said, and sealed his lips around the head, sucking and licking until he felt Will’s dick jump and pulse cum onto his tongue. He pulled away reflexively, and scrabbled for the Kleenex on the bedside table. He spat into it a couple times.

“Sorry,” Will said.

“It just—surprised me,” Dean said, wiping his lips. 

“There’s mouthwash in the bathroom, down the hall.”

Dean nodded and got up, pulling his pants up. He found the mouthwash in the medicine cupboard and rinsed thoroughly, mentally congratulating every girl he’d known who’d swallowed.

He went back into the bedroom, and hovered by the door. Will was sprawled out on the bed. “You can stay if you want,” he said sleepily.

“I have to get up early,” Dean said, “Hit the road.”

“Well, I’m sleeping in and avoiding the shit downstairs for as long as possible,” Will said, rolling over, “So don’t wake me up, but the offer still stands.”

Dean hesitated, then stripped off his jeans and climbed onto the opposite side of the bed. Will fumbled with the lamp and turned it off, breath already slowing and evening out, and Dean closed his eyes.

New Haven, Connecticut  
September 9, 2004

“Hi,” the guy said brightly. Dean ran his eyes over the plaid shirt, neat beard, and chunky glasses and grimaced.

“Look,” he said, cutting off whatever the guy was about to say, “I’m just looking for the admissions office.” He was sure there should be some kind of a student directory online, but he couldn’t find the fucking thing, and now he was wading through kids, who were all handing out flyers for their stupid clubs, and he couldn’t find the fucking admissions office either.

“Oh, it’s just on your left there. The white building with the columns,” the guy said, pressing a flyer into his hands at the same time. “And I hope you’ll consider checking out the LGBT Co-op!”

Dean frowned at him, and then leaned in and hissed, “Do I look gay?” 

“What?” the guy said.

“This is the third time someone has given me one of these!” Dean said, waving the flyer.

“Oh,” said the guy. “No one ‘looks gay’. We try to distribute our flyers to as many students as possible, so that hopefully they reach the people they need to.”

“Right,” Dean said, shoving the flyer into his pocket. “Well, I’m not a student. I’m from Animal Control, actually.”

“Oh, this is about those weird attacks in the park?” the guy said. “I can’t comment on that,” Dean said.

The guy shifted the flyers and stuck out his hand. “I’m Luis.”

“Brian Scott,” Dean said, shaking his hands. “Thanks for your help.”

“Sure,” Luis said, “Good luck.”

Dean nodded and cut across the lawn towards the white building.

Admissions was too official for Dean’s taste. Give him a backwaters Sheriff's office and he could lie his way into or out of anything, but these guys were all forms and computers and “let me just call and confirm” like they could see right through him. Dean wondered how Sam ever got into Stanford if it was like this.

By the time Dean got out, it was cooling off, but he had the names and information he needed tucked under one arm. Luis was still hanging around by the road, and he looked Dean up and down appreciatively, smiling. Dean gave him a look that was supposed to be a glare but obviously sent a different message, because Luis was jogging over to him.

“You know I was thinking about going to grab a coffee,” he said.

“Now you do think I’m gay,” Dean said. Luis shrugged. “You’re gay, though.”

“I’m bisexual, actually,” Luis said.

“Isn’t that just a cop-out?”

“See, I can’t tell if you’re an asshole or just closeted.”

Dean cringed. Luis held his hands up, palms out, the same way hunters did to spooked civilians.

“Come on,” he said. “Just coffee. We’ll get it from a coffee stand too; we won’t even sit or anything.”

“Why?” Dean said.

“My hands are cold,” Luis said. “And, okay, I was maybe also going to offer to go back to my place and mess around, because I am a complete stereotype and am just that easy, but I have roommates and everything, so I feel like that would freak you out.”

Dean readjusted the papers he was holding. “Maybe I could drive you home,” he said.

“Thanks,” Luis said, grinning, “But when I moved out I promised my mom I wouldn’t get into cars with strange men.”

“Hey,” Dean said, “It’s not like I drive a white van with blackout windows.” 

“I dunno, man,” Luis said, pushing his glasses up, “Animal Control types are a little creepy, even if they’re as hot as you.”

“I’m offended.”

“Sorry, I won’t call you hot again, then.”

Dean snorted.

“C’mon,” Luis said, “Coffee.”

“Alright,” Dean said, letting Luis lead the way down the street.

“So how come you’re in animal control?” Luis asked. “It is kind of weird.” 

“It’s a long story,” Dean said.

“Try me.”

“It’s kind of the family business, I guess. A my-dad-did-it-before-me kind of thing. And high school wasn’t really for me, so it made sense.”

“Does it still make sense?”

“As much as anything else does. So you’re really into the whole being bisexual thing, huh?” Dean said, gesturing at the pamphlets.

“I guess I am now, yeah,” Luis said. “Now?” Dean asked. 

“ _That’s_ a long story.” 

“Try me.”

Luis sighed and glanced at him. “I’ve got a little sister, you know? And we’re both pretty smart, but there was just no fucking way our family was going to get us both through university, especially not a place like this. I didn’t have any plans, so I figured I’d do the military thing. I had cousins in the army, and my mom was okay with it, as long as I got a good education for myself too. But then, long story short, someone asked, and I told, and I’m on my own for my last year. I’ve got some savings for my sister, but it kind of changed things.” He glanced at Dean again. “For example, I started growing this beard.”

Dean laughed quietly, and Luis gestured towards the coffee stand to their right.

“Let me get this,” Dean said, pulling out his wallet. Luis gave him a look. “I’ve got a little brother,” he said, shrugging.

Luis’ lips twitched. “Medium, two sugars, please,” he said. “And a medium, black,” Dean said, pulling out a twenty.

“Thanks,” Luis said, wrapping his hands around his coffee while Dean accepted his change from the smiling woman at the cash. “Want to see something cool?”

“Sure,” Dean said cautiously.

“Come on,” Luis said, leading him across the grass to where two buildings joined, or almost joined. There was a space between them, and Dean eyed Luis doubtfully as he squeezed in. “Just come on,” Luis said. Dean surreptitiously checked that he could get to his knife, and then squeezed through after him.

It was a tiny space, about three feet by four feet, completely enclosed by the buildings on either side, and it was noticeably warmer than it was outside. Dean eyed the vents set in one of the walls, which he assumed were pumping out some kind of heat.

“Backs onto a kitchen, so it’s always warmer in here, even in the winter,” Luis said, leaning against the wall.

“How’d you find this?” Dean asked.

Luis laughed. “Guy brought me in here so I could give him a handjob. Not that he returned the favour.”

“Dick,” Dean said, sipping his coffee. Luis laughed again, setting the flyers down carefully on the ground.

Dean gulped down some more of the coffee, which was pretty shitty. Fucking universities. “So let me make it up to you,” he said.

“Huh?” Luis said, glancing up.

Dean crossed the space easily and pressed his palm to Luis’ crotch. “Oh,” Luis said. “Sure. Yes. Please.”

Dean snorted and rubbed his hand across the line of Luis’ dick, leaning in and kissing him messily, tasting more shitty coffee and ignoring the weirdness of the beard, until he was hard under Dean’s hand. He pulled away enough to get Luis’ pants open and his dick out, spat in his hand for good measure, and started stroking, tightening his grip when Luis’ mouth fell open.

“This is probably why people think you’re gay,” Luis said, hitching his hips forward.

Dean’s hand stuttered, and then he sped up. “Smart ass.”

“Sorry,” Luis said, smiling as his eyes slid shut, “Oh, fuck, do that again.” Dean smirked and he rubbed his thumb across the slit on the upstroke.  
Luis panted, and arched his hips forward until only his shoulders were touching the wall, and then came all over Dean’s hand, swinging an arm up to press against the wall and knocking Dean’s coffee out of his free hand.

“Shit, sorry,” he panted, sagging back against the wall. 

“S’okay,” Dean said, “It went all over your flyers though.”

“Fuck ‘em,” Luis said, opening his eyes and hooking a finger in Dean’s jeans. “You want me to?”

“It’s okay,” Dean said, “Just, I don’t know, pay it forward or something.” Luis laughed and did up his pants.

Seattle, Washington  
July 17, 2005

Dean hated hunts in cities. He hated the people, and the noise, and the thousand places something could be hiding, and no space to park the Impala without worrying someone was going to mess her up, and the extra shitty motels where you actually had to walk past the desk to get to your room and just hope the night clerk didn’t want to know why you were covered in grave dirt or intestines or dark orange slime.

Right now he really hated the motels, because Cindi (with an _i_ ), who five minutes ago had been staring at Dean like she wanted to eat him, was now looking at him like maybe he wanted to eat her, after killing her and cutting her up into tiny pieces.

“I’m just going to get a cab home,” she said, backing out of the lobby. Dean sighed, and followed her out to make sure she got a cab. When he came back into the lobby, the night clerk looked up at him, turning a page in his book, and said, “I get off work in ten minutes.” 

“What?” Dean said stupidly.

“I said I get off work in ten minutes,” the guy repeated, staring at Dean pointedly.

“Oh,” Dean said, looking the guy over more closely. He was small, thin- looking even in the baggy hoodie he had on. He had his fingernails painted red and Dean was pretty sure he was wearing eyeliner. He was staring at Dean like he was bored by the whole conversation, but Dean could see the white of his knuckles where they curled around his book. He was reading _A Wrinkle in Time_. “I’m in room eight.”

The guy nodded and bent over his book. Dean hovered for a minute, wondering if he’d misunderstood, before he went back to his room. He’d already put away anything that could look weird, since he had been planning on maybe bringing someone back, so he slipped off his boots and started flipping through channels with the volume muted. 

He was watching some sort of low-budget cooking show when there was a knock on the door. He got up and unlocked and opened it.

“Room service,” the guy said, looking up at Dean and pushing his hair out of his eyes. 

Dean laughed sharply and stood aside to let him in. “I’m Dean,” he offered. 

“Milo,” the guy said, dropping his bag against the wall. Dean nodded vaguely, switching the TV off and sitting on the edge of the bed. Milo pulled off the hoodie, leaving himself in a thin T-shirt and ragged cutoffs, and climbed onto Dean’s lap. 

“This good?” he said, inches from Dean’s mouth, hitching closer and rubbing his ass against Dean’s cock. 

“Sure,” Dean said, settling his hand’s on Milo’s waist and kissing him. Milo licked at his tongue, looping his arms around Dean’s neck and grinding down harder as he rolled his hips. Dean moved one hand to Milo’s jaw, pressing gently until he opened wider for Dean’s tongue. 

Milo broke away, licking at the hinge of Dean’s jaw. “I want to ride you until you come,” he whispered, pressing his mouth close to Dean’s ear. Dean stood them both up abruptly and started stripping Milo. 

“You have lube?” Dean asked, attacking his own clothes. Milo crouched down naked to dig around in the pocket of the hoodie, and came up with a condom and a couple silver packets. 

Dean got on the bed, shoving the pillows into a pile against the headboard and leaning back. Milo straddled his legs, tearing open one of the packets and pouring the lube over two of Dean’s fingers before shuffling forward and guiding Dean’s hand behind him. 

Dean slid his fingers down until Milo shoved his hips back when one fingertip rubbed up against his hole. Milo nodded, reaching down to stroke Dean’s half-hard cock. Dean pushed his finger in slowly, watching Milo’s face, and started to slide it in and out slowly. 

“Another, another,” Milo said, pushing back again. Dean worked another finger in slowly next to the first one, twisting and crooking them as Milo relaxed around them, and then fucking them in and out. He looked down to where Milo was stroking him, saw the red nails bright against Milo’s skin, and thrust his hips up. Milo moved his hand faster and nodded again. “Another,” he said. Dean pulled his fingers out, grabbed the other packet of lube, and spread it over three of his fingers. Milo exhaled heavily when he pressed them back in, hips jerking forward and then back onto Dean’s hand, and Dean went back to stroking with his fingers, trying to find the right spot. When Milo finally gasped, he pushed down on the same place. Milo screwed up his face, panting, and reached blindly for the condom. 

He squirmed away from Dean’s fingers, rolled the condom down, and then pushed his mouth over Dean’s dick messily, once and then twice more. 

“Come on,” Dean muttered, tugging on his hair. Milo straddled his hips, reached behind him, and sank down onto Dean’s dick, pausing halfway to rock slightly before pushing all the way down. Dean exhaled roughly, hips tight against Milo’s ass. Milo braced his hands on Dean’s ribs and his feet against the mattress, and lifted himself up. Dean fisted his hands in the blanket and Milo sank back down, twisting his hips as he did. 

“Motherfuck,” Dean said, pressing his feet into the mattress to thrust up as Milo dropped down again. He pulled himself together enough to wrap a hand around Milo’s dick, shifting his hand until he figured out a rhythm, stroking down as Milo pushed up. 

Dean could feel Milo’s legs starting to tremble against his hips as he rode Dean, flexing and twisting like he was trying to get Dean’s cock right where he wanted it. Dean could feel the heat building in his groin and bit down on his lip furiously, tightening his grip on Milo. 

When he came, he grabbed Milo by the hips and ground up into him, as deep as he could. Milo replaced Dean’s hand with his own, stripping his dick frantically, watching as Dean relaxed underneath him and finally coming across Dean’s stomach. 

Dean had drawn his knees up behind Milo, and Milo leaned back against them for a minute before climbing off of Dean. 

Dean sat up on the edge of the bed to slide the condom off while Milo pulled his clothes on slowly. Some of Milo’s come slid down his stomach, cool against his skin, and he wiped it off hastily with the sheet, grimacing. 

“Nice meeting you, Dean,” Milo said, grabbing his bag and letting himself out. 

Rawlins, Wyoming  
October 24, 2005 

It took seven of them to clean out the entire nest of ghouls, and hunters don’t do well in groups that big, but it was a job well done, so they went to a bar after. Dean had worked with two of them before, but the other four were just guys who knew Pastor Jim. Dean was by far the youngest, which meant the others had decided to “educate” Dean, despite the fact that Dean had been training since he was six and half of these guys didn’t do much more than put down a few ghosts on the weekends. 

“I’ll get the next round,” Dean said firmly, after a long rambling anecdote about how you never knew when holy water was going to come in handy. 

“Seven of the same,” he said to the bartender, who nodded and shuffled down to the other end of the bar to get the whisky. Dean wondered how soon he could leave without being pegged as rude or weird. 

“Hey,” said a guy, packing the word with come-on and sliding onto the stool next to him. “I’m Kyle. Why don’t you ditch those guys and come have a drink with me?” 

Dean glanced briefly at him out of the corner of his eye. “Not gonna happen, Kyle. Those guys would not be impressed. Get out of here.” 

“Aw,” Kyle said, because he was clearly an idiot, “I’m not afraid of them.” 

And Dean has had enough, because he’s spent the last three hours faking a smile, and the three days before that choking on grave dust and decay, and the five days before that without talking to anyone except waitresses and gas station cashiers, so he slams a handful of cash down on the bar, grabs the tray that the bartender is sliding across to him, and spits, “Well, I am,” before turning and going back to their table. 

The others are trading legends of vampires and paying no attention to anything else. Dean passes the drinks around, makes a joke about _Dracula_ and not one about _Buffy_ , and sits down, deciding he’ll give it another hour. 

On his way out to the car, he flips open his phone and dials his dad. It rings through to voicemail, which isn’t that unusual lately. 

“Hey dad,” he said, leaning against the Impala. “Finished up the ghouls. Went fine. Andy Moreau says to tell you you still owe him fifty bucks. Let me know when you get this.” 

He shut the phone and unlocked the car. He should hear from him in a day or two at the latest, their standard I-didn’t-die-on-the-case phone call; the Jericho thing had sounded like a pretty standard haunting. 


End file.
